Cheapest flights to Chicago are generally available in April whilst July tends to be most expensive

Popular airports

Flights to Chicago land at the airports Midway (MDW),
O'Hare Intl (ORD) and
Executive Airport (PWK).

About Chicago

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Chicago’s explosive forward motion radiates off every city block, the legacy of a city that grew from a podunk frontier town to a sprawling metropolis in only 60 years. The vestiges of this growth are still visible in the city’s architecture, where turn-of-the-century romance rubs up against sleek modern towers of steel and glass.

Chicago's nicknames include: Windy City, Second City, the City That Works, and the City of Big Shoulders.

A cultural hub in its own right, Chicago is home to world-class art museums, a historically important and still swingin’ jazz scene – and more professional sports teams than you could swing a bat at. Add to this some of the best improv comedy in the US, and of course, its own special brand of comfort food – deep dish pizza and hot dogs topped with vegetables in place of the usual relishes – and you have plenty of entertainment to go around.

The Chicago River is the only river in the world to flow backwards, after engineers reversed it in 1900 to improve sanitation.

About Chicago

For modern-day gangsters and molls, Chicago is the perfect backdrop for wild good times. Sure there’s art and architecture aplenty, but it’s when the sun goes down that the city really starts to swing.

Powering north along Lakeshore Drive, the Magnificent Mile appears like a comic-book version of a city – the sort of glossy metropolis in which Superman or Batman might battle supervillans. Neo-Classical civic buildings stand in the shadows of ultramodern skyscrapers, with Lake Michigan glittering in the background. Seen from above, the nocturnal city is a perfectly plotted grid of lights. Instead of paying to stand in line and gawp at the view, take the elevator to the 96th floor of the iconic Hancock Centre and drink it in with a martini in your hand.

For all its glamour, Chicago is a city of brash extremes. In winter, come prepared for snow – and lots of it. In the summer, you’ll be glad of the famous breeze coming off the lake. Year-round, hardy locals jog and cycle along the Millennium Park, which in the summer months play host to a succession of open-air festivals.

There are plenty of pricey downtown bars that promise an authentic Chicago Blues experience, but if you’re after the real deal you’ll want to head to the southside neighbourhood joints. Here the vibe’s a little edgier and the music is world-class. If you’re more into clubbing, the ultra-luxe Gold Coast neighbourhood lives up to its name, while hipsters might prefer the dive bars of Bucktown, Wicker Park, or the Ukrainian Village. These days leafy Lincoln Park is ‘Stroller Central’, but up north in Boystown you’re more likely to find go-go dancers than baby-changing facilities.

While Chicago is rightly celebrated for its museums, there’s one piece of living history that you shouldn’t miss: Wrigley Field. Even if you’re a total strikeout when it comes to baseball, a trip to the historic stadium is worth if for the atmosphere alone. Grab yourself an over-sized beer and a hotdog, and remember to cheer for the Cubs … and for the boisterous, blowsy, fun-loving Windy City itself.